Conformational Analysis of [3.3]Paracyclophane | Zendy

Sako Katsuya | Zendy; Meno Tatsuya | Zendy; Shinmyozu Teruo | Zendy; Inazu Takahiko | Zendy; Takemura Hiroyuki | Zendy

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Conformational Analysis of [3.3]Paracyclophane

Author(s) -

Sako Katsuya,

Meno Tatsuya,

Shinmyozu Teruo,

Inazu Takahiko,

Takemura Hiroyuki

Publication year - 1990

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19901230334

Subject(s) - conformational isomerism , chemistry , cyclohexane conformation , cyclophane , crystallography , stereochemistry , crystal structure , molecule , organic chemistry , hydrogen bond

According to a VT‐NMR study, [2,2,11,11‐D 4 ][3.3]paracyclophane ( 1‐D 4 ) exists as a mixture of chair and boat conformers in the ratio of 1.0: 1.3 (ΔG o = 0.1 kcal/mol) at ‐70°C with an energy barrier for the chair‐boat inversion of 12.0 kcal/mol (270 MHz, ca. 1% CD 2 Cl 2 solution, T c = ‐ 15°C). The conformer ratio (chair/boat) is dependent on the concentration of 1‐D 4 ; it is 1:1 in ca. 1% CD 2 Cl 2 solution but 1:2 in ca. 5% CD 2 Cl 2 solution, due to preferential crystallization of the chair conformer.

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